Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy Tetraglucosylcalix[4]arene

Torvinen, Mika; Kalenius, Elina; Sansone, Francesco; Casnati, Alessandro; Jänis, Janne

doi:10.1007/s13361-011-0289-3

Cited by 16 publications

(12 citation statements)

References 72 publications

(96 reference statements)

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“…Collision‐induced dissociation (CID) experiments were used to investigate the relative gas‐phase kinetic stability of complexes, which can be expressed as E COM 50% based on a dissociation curve calculated considering the relative intensities of the adduct and of the dissociation products in the mass spectrum at different collision energy values (see Figure S29, S32, S33, S35, S36 and S38‐S43 in the Supporting Information for spectra and dissociation curves) . Since the formation of 1:1 and 2:1 ligand/DNA complexes were observed in most of the cases, the stability of the complexes with different stoichiometry was investigated.…”

Section: Chemical Structures Of Compounds 4a–4fmentioning

confidence: 99%

Synthesis via A3 Coupling Reaction of Anthracene‐Propargylamine as a New Scaffold for the Interaction with DNA

et al. 2019

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A series of new anthracene‐propargylamine derivatives were obtained through an efficient synthesis based on the A3 coupling reaction. This set of planar molecules were designed to bind double stranded and G‐quadruplex DNA arrangements. Their interaction pattern of the small molecules with DNA was predicted by molecular docking and their theoretical pharmacokinetic properties were calculated, giving encouraging results in terms of drug‐likeness. The general preference for double stranded DNA suggested by docking experiments was supported by a set of electrospray ionization mass spectrometry (ESI‐MS) experiments.

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Section: Chemical Structures Of Compounds 4a–4fmentioning

confidence: 99%

Synthesis via A3 Coupling Reaction of Anthracene‐Propargylamine as a New Scaffold for the Interaction with DNA

et al. 2019

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“…Although p-p and cation-p interactions are considered to provide an essential contribution to the observed binding selectivity for serotonin over norepinephrine, epinephrine and dopamine, the results obtained strongly indicate that the calixarene complexes are mainly stabilised by H-bonds. 55 Diglucosyl-24a and tetraglucosylthioureido calix [4]arene 24b also bind amino acids forming only 1 : 1 complexes with a marked selectivity for aromatic amino acids (stability order: Trp, Tyr c Phe > Ser, Leu, Asp). Computational studies proved the presence of H-bonds between saccharide units and the indole N atom of Trp or the phenolic hydroxyl group of Tyr, at least in the gas-phase.…”

Section: Glycocalixarenes and Multitaskingmentioning

confidence: 99%

Multivalent glycocalixarenes for recognition of biological macromolecules: glycocalyx mimics capable of multitasking

2013

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The glycoside cluster effect, a special case of multivalency involving carbohydrates, is a powerful tool exploited by Nature to make relatively weak interactions stronger and more specific. Organic and supramolecular chemists have been applying this concept and are devising a plethora of neo-glycoconjugates which can interfere with a series of pathological events such as infections due to viruses and bacteria, tumour progression and migration, and inflammation processes. In the present Tutorial Review, we will illustrate the factors that make calixarenes, the cyclic oligomers obtained by the condensation of phenols/resorcinols and aldehydes, unique scaffolds for the construction of multivalent glycosylated ligands, individually analysing how structural parameters such as the size, valency, conformation, self-assembling behaviour of the macrocycle and especially the topology of the saccharide presentation in space influence the biological properties. We will not only survey the most significant results obtained to date in the inhibition of carbohydrate binding proteins (lectins), but we will also try to paint a picture of the potential that multivalent glycocalixarenes might have in bionanotechnology and nanomedicine, that are especially related to their combined ability to load cargo and to specifically deliver that cargo to target cells.

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“…31 Again, the value of E COM 50% can be directly calculated by using the relative intensities of such complexes and fragmentation products by plotting dissociation curves and using the following formula: E COM = I complex /(I complex + I dissociation products ) (Figure 4). 31,119 This parameter is of great relevance when evaluating small molecules as GQ binders, as GQ stabilization is one of the required properties for triggering biological effects. 31 The issue of complex stability can be also approached by means of ESI-MS from another perspective.…”

Section: ■ Introductionmentioning

confidence: 99%

Combining Electrospray Mass Spectrometry (ESI-MS) and Computational Techniques in the Assessment of G-Quadruplex Ligands: A Hybrid Approach to Optimize Hit Discovery

et al. 2021

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Guanine-rich sequences forming G-quadruplexes (GQs) are present in several genomes, ranging from viral to human. Given their peculiar localization, the induction of GQ formation or GQ stabilization with small molecules represents a strategy for interfering with crucial biological functions. Investigating the recognition event at the molecular level, with the aim of fully understanding the triggered pharmacological effects, is challenging. Native electrospray ionization mass spectrometry (ESI-MS) is being optimized to study these noncovalent assemblies. Quantitative parameters retrieved from ESI-MS studies, such as binding affinity, the equilibrium binding constant, and sequence selectivity, will be overviewed. Computational experiments supporting the ESI-MS investigation and boosting its efficiency in the search for GQ ligands will also be discussed with practical examples. The combination of ESI-MS and in silico techniques in a hybrid high-throughput-screening workflow represents a valuable tool for the medicinal chemist, providing data on the quantitative and structural aspects of ligand–GQ interactions.

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Noncovalent Complexation of Monoamine Neurotransmitters and Related Ammonium Ions by Tetramethoxy Tetraglucosylcalix[4]arene

Cited by 16 publications

References 72 publications

Synthesis via A3 Coupling Reaction of Anthracene‐Propargylamine as a New Scaffold for the Interaction with DNA

Synthesis via A3 Coupling Reaction of Anthracene‐Propargylamine as a New Scaffold for the Interaction with DNA

Multivalent glycocalixarenes for recognition of biological macromolecules: glycocalyx mimics capable of multitasking

Combining Electrospray Mass Spectrometry (ESI-MS) and Computational Techniques in the Assessment of G-Quadruplex Ligands: A Hybrid Approach to Optimize Hit Discovery

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